Potassium Iodide → HCID 14230181, compound

HRID 35341Notes

Reaction equation

HRID 35341 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH:13]2[C:18]([NH2:20])=[O:19])=[CH:4][CH:3]=1.Cl[CH2:29][CH2:30][C:31]([NH:33][C:34]1[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:41])=[O:32].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[NH2:20][C:18]([CH:13]1[N:12]([CH2:11][CH2:10][CH2:9][CH:8]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:17][CH2:16][N:15]([CH2:29][CH2:30][C:31]([NH:33][C:34]2[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:41])=[O:32])[CH2:14]1)=[O:19]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 45508323-Chloro-2',6'-propionoxylidideHCID 138832881-[4,4-Bis(4-fluorophenyl)butyl]-2-piperazinecarboxamide

Product 1

HCID 14230181HCID 14230181, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.7 parts of 1-[4,4-bis(4-fluorophenyl)butyl]-2-piperazinecarboxamide, 2.3 parts of 3-chloro-N-(2,6-dimethylphenyl)propanamide, 2.1 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 parts of 4-methyl-2-pentanone was stirred and refluxed for 20 hours using a water-separator. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue solidified on triturating in 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.87 parts (70.8%) of 3-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethylphenyl)-1-piperazinepropanamide; mp. 120.9° C. (compound 122)

Workup

  1. temperaturerefluxed for 20 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customThe oily residue was purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customon triturating in 2,2'-oxybispropane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-78494dc96eda43ba92e7924d4d4763f5
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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